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Issue 7, 2000
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Synthesis of perfluoroalkylated sugars catalyzed by rabbit muscle aldolase (RAMA)

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Abstract

Perfluoroalkyl iodides [RfI: Cl(CF2)4I, Cl(CF2)6I, C8F17I] react with acrolein diethyl acetal catalyzed by sulfinatodehalogenation reagents to produce 2-iodo-3-(perfluoroalkyl)propanal diethyl acetal 1, which is converted into (E )-3-(perfluoroalkyl)acrolein diethyl acetals 2 on treatment by base (KOHMeOH). 3-Perfluoroalkyl-D-glyceraldehyde diethyl acetals 3 are produced through the asymmetric dihydroxylation (AD) of compound 2. Then 3 are easily hydrolyzed to 3-perfluoroalkyl-D-glyceraldehydes 4, which could react with DHAP catalyzed by RAMA and further acid phosphatase to form 6-C-perfluoroalkyl-D-fructose, which is a novel sugar and surfactant.

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Publication details

The article was received on 23 Dec 1999, accepted on 21 Feb 2000 and first published on 23 Mar 2000


Article type: Paper
DOI: 10.1039/A910336H
Citation: J. Chem. Soc., Perkin Trans. 1, 2000,0, 1105-1108
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    Synthesis of perfluoroalkylated sugars catalyzed by rabbit muscle aldolase (RAMA)

    W. Zhu and Z. Li, J. Chem. Soc., Perkin Trans. 1, 2000, 0, 1105
    DOI: 10.1039/A910336H

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